23+ Stylish Messy Ponytail Hairstyles

The messy ponytail has evolved from a lazy day hairstyle to a runway-worthy look embraced by celebrities and fashion icons worldwide. It’s that perfect balance of effortless chic that somehow says “I woke up like this” while still looking absolutely intentional. I’ve spent years obsessing over the perfect undone pony, and lemme tell you—there’s an art to making something look artfully disheveled.

Whether you’re rushing to work, heading to brunch, or attending a formal event, a strategically messy ponytail can be your go-to style. The beauty lies in its versatility and the fact that it actually looks better with a bit of lived-in texture. Ain’t nobody got time for perfectly smooth, sleek styles everyday anyways!

So let’s dive into 23+ messy ponytail variations that’ll revolutionize your hair game. These styles work for different hair lengths, textures, and occasions. Trust me, your boring old ponytail is about to get a major upgrade.

1. The Classic Textured Pony

1. The Classic Textured Pony

The foundation of all messy ponytails starts here. Gather your hair at the middle of the back of your head, secure with an elastic, then gently pull pieces loose around your face. The key is to tease the ponytail slightly for added volume and pull on the crown for height.

This style works amazingly for second-day hair when you’ve got natural texture working in your favor. Pro tip: rub a tiny bit of texturizing powder between your fingers before messing up the crown for extra staying power.

2. Low Messy Knot

2. Low Messy Knot

For an effortlessly cool vibe, the low messy knot sits just above your neckline. Start by gathering hair at the nape, twist loosely, then wrap and secure with bobby pins rather than an elastic for that undone feel.

This style is perfect for those with medium to long layers, as shorter pieces will naturally fall out to frame your face. It’s my go-to for dinner dates when I want to look like I’ve made an effort but didn’t try too hard, ya know?

3. Half-Up Messy Pony

3. Half-Up Messy Pony

The half-up messy pony combines the best of both worlds—hair down with the practicality of a ponytail. Take just the top section of your hair, from temples back, and secure it high on your crown.

Tease the ponytail portion and leave plenty of volume at the roots. This style is gorgeous for showing off highlights or balayage, as it creates dimension with the different sections. Works amazing for those days when you can’t decide between wearing your hair up or down!

4. Side-Swept Messy Pony

4. Side-Swept Messy Pony

Give your ponytail an asymmetrical edge by placing it slightly off-center. Create a deep side part, then gather your hair to the opposite side at ear level. The contrast between the sleek part and the messiness of the pony creates an interesting visual dynamic.

This style is surprisingly flattering on most face shapes and adds a bit of drama without much effort. I always reach for this when I’m feeling a bit edgy but still need something practical for my workday.

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5. Bubble Messy Ponytail

5. Bubble Messy Ponytail

Take your messy pony to the next level by creating sections. After securing your initial ponytail, add hair ties every 1-2 inches down the length, gently tugging each section outward to create “bubbles.”

The messier and more imperfect each bubble, the cooler this style looks. It’s deceptively simple but gets compliments every single time I wear it. Perfect for festivals or anytime you wanna stand out from the regular ponytail crowd!

6. Braided Messy Ponytail

6. Braided Messy Ponytail

Start with a standard messy pony, then divide the tail into three sections and create a loose braid. The key is not to braid too tightly—you want it to look a bit undone and ready to unravel.

Pull on the edges of the braid to roughen it up even more, and don’t worry if pieces fall out. This style has saved me countless times when my hair needs washing but I still wanna look put-together for an important meeting.

7. Volumized Crown Pony

7. Volumized Crown Pony

If your hair tends to fall flat, this ponytail variation will be your new bestie. Start by backcombing the crown section aggressively, then smooth just the surface before gathering everything into a mid-height ponytail.

The contrast between the voluminous crown and the relatively tame ponytail creates a silhouette that’s reminiscent of 60s bouffant styles but with a modern, messier approach. This one’s my secret weapon for days when my hair just won’t cooperate!

8. Wrapped Messy Ponytail

8. Wrapped Messy Ponytail

Elevate a basic messy pony by using a small section of your own hair to hide the elastic. After securing your ponytail, take a thin strand from underneath, wrap it around the base several times, then secure with a bobby pin.

This small detail makes a huge difference in how polished your messy style appears. It’s those little touches that make people wonder how you always look so effortlessly stylish, even with just a simple pony!

9. Twisted Side Messy Pony

9. Twisted Side Messy Pony

For a romantic take on the messy ponytail, try incorporating twists. Create a deep side part, then take 1-inch sections from along your hairline and twist them back, adding hair as you go (similar to a French braid but twisting instead).

Continue until you reach the opposite ear, then gather everything into a low side ponytail. The combination of twisted sections with messy texture creates beautiful dimension. I’ve worn this to weddings and gotten so many questions about who did my hair!

10. Messy Pony with Bandana

10. Messy Pony with Bandana

Add a retro touch to your messy ponytail by incorporating a bandana or scarf. Fold your chosen fabric into a band, place it at your hairline, tie at the nape, then create your messy pony just below the knot.

This style not only looks cute but serves the practical purpose of keeping hair off your face on hot days. Plus, it’s a great way to incorporate a pop of color or pattern into your look. I’m obsessed with this for summer outings!

11. Slept-In Messy Pony

11. Slept-In Messy Pony

This deliberately undone style celebrates texture and imperfection. Start with completely dry, preferably day-old hair. Flip your head upside down, roughly gather your hair with your fingers (not a brush!), and secure with an elastic placed slightly off-center.

The beauty of this style is that it should look like you literally just rolled out of bed and haphazardly pulled your hair back. Sometimes the messiest styles are the most difficult to perfect, which is kinda ironic, innit?

12. Knotted Messy Ponytail

12. Knotted Messy Ponytail

Instead of using an elastic, try knotting your hair for a truly unique ponytail. Divide your gathered hair into two sections, tie them in a simple knot (like the first step when tying shoelaces), then continue with another knot before securing the ends with a small clear elastic.

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This technique works best on longer hair and creates an interesting textural element that standard ponytails lack. It takes practice but is totally worth mastering for those days when you want something different!

13. Crimped Messy Ponytail

13. Crimped Messy Ponytail

Bring back the crimped texture trend with this funky ponytail variation. Before gathering your hair, use a crimping iron on random sections throughout your hair. Don’t crimp everything—the contrast between smooth and crimped creates the perfect messy texture.

Once crimped, pull into a high ponytail, allowing the textured sections to create natural volume and interest. This unexpected texture makes even a simple ponytail look editorial and fashion-forward. Total game-changer when I’m bored with my usual styles!

14. Accessorized Messy Pony

14. Accessorized Messy Pony

Sometimes, the perfect finishing touch for a messy ponytail is a well-chosen accessory. Secure your messy pony as usual, then add a statement hair clip, a row of small clips, or even delicate hair rings threaded onto sections of the ponytail.

The juxtaposition of messy hair with something sparkly or structured creates a beautiful contrast. I’ve started collecting unique hair accessories specifically for elevating my lazy-day ponytails into something special!

15. Messy Ponytail with Curtain Bangs

15. Messy Ponytail with Curtain Bangs

If you have bangs, incorporate them into your messy ponytail for a face-framing effect. Pull your hair back loosely, allowing your curtain bangs or face-framing layers to fall naturally around your face.

The combination of the messy ponytail with the softness of bangs creates a flattering frame that highlights your facial features. This has become my signature look since growing out my bangs—it’s the perfect balance of practical and pretty!

16. Teased Root Messy Pony

16. Teased Root Messy Pony

For a punk-inspired take on the messy ponytail, focus on creating dramatic volume at the roots. Section off the top portion of your hair, tease it aggressively, then smooth just the surface before gathering everything into a mid-height ponytail.

The extreme contrast between the voluminous crown and the relatively tame ponytail creates a silhouette that’s edgy yet still wearable. Don’t be shy with the teasing—go big or go home with this style!

17. Double Messy Ponytails

17. Double Messy Ponytails

Channel your inner fashionista with double messy ponytails positioned one above the other. Section your hair horizontally from ear to ear, create a messy pony with the top section, then gather the remaining hair into a second pony just below the first.

This playful style looks especially cool when both ponytails are deliberately messy and textured. It’s unexpected on adults and always earns me style points when I’m feeling brave enough to rock it!

18. Wet-Look Messy Ponytail

18. Wet-Look Messy Ponytail

Combine the trendy wet-look style with a messy ponytail for an editorial vibe. Apply gel or mousse to damp hair, focusing on the roots and mid-lengths, then comb through with your fingers for that just-out-of-the-shower texture.

Gather into a low or mid-height ponytail, allowing some pieces to fall around your face. The contrast between the sleek, wet-looking roots and the drier, messier ends creates a modern, high-fashion ponytail that’s surprisingly wearable. Perfect for making a statement at special events!

19. Messy Fishtail Ponytail

19. Messy Fishtail Ponytail

Elevate your ponytail with a loose fishtail braid. After securing your pony, divide it into two sections and create a fishtail braid, being careful not to pull too tightly. Once braided, gently tug at the edges to loosen and roughen the texture.

This style works beautifully for special occasions when you want something more elaborate than a standard ponytail but still with that effortless, undone quality. The intricate texture of the fishtail adds beautiful dimension to the messiness!

20. Super-High Messy Pony

20. Super-High Messy Pony

Channel your inner Ariana Grande with a super-high messy ponytail positioned at the crown of your head. The height elongates your face and creates a youthful, playful silhouette that still manages to look sophisticated when paired with the right outfit.

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After securing, tease the ponytail itself for added volume and pull gently at the roots to loosen and create height. This style looks particularly striking with long hair and creates a dramatic profile that’s perfect for making an entrance!

21. Twisted Rope Messy Pony

21. Twisted Rope Messy Pony

Instead of a standard ponytail, try a twisted rope technique for added interest. After gathering your hair, divide it into two sections and twist each section clockwise, then twist them together counterclockwise to create a rope effect.

Secure at the end and pull gently at the twists to loosen and create messiness. This technique adds texture and prevents your ponytail from looking too ordinary. I love how this style holds its shape throughout the day without looking too “done.”

22. Curly Messy Ponytail

22. Curly Messy Ponytail

Embrace your natural curls or add some with a curling iron before creating your messy ponytail. The key to a great curly pony is positioning—try placing it slightly lower than you would a straight ponytail to prevent too much volume at the crown.

Gently gather your curls without brushing (use your fingers instead!) to maintain their integrity and shape. Let curly tendrils fall around your face for that perfectly imperfect finish. This style celebrates texture rather than trying to control it!

23. Messy Pony with Hair Scarf

23. Messy Pony with Hair Scarf

Wrap a colorful silk scarf around your messy ponytail for a touch of vintage-inspired glamour. After securing your pony, fold a narrow scarf lengthwise and wrap it around the base, tying it in a small knot or bow underneath.

Allow the ends of the scarf to blend with your hair for an integrated look. This simple addition transforms a basic messy ponytail into something special and provides an opportunity to coordinate with your outfit or add a pop of unexpected color.

24. Sleek Front, Messy Back Ponytail

24. Sleek Front, Messy Back Ponytail

Create an interesting contrast by keeping the front sections of your hair sleek and smooth while allowing the ponytail itself to be deliberately messy. Use a fine-tooth comb and some gel to slick back the front and sides before gathering everything into a ponytail.

Once secured, mess up the ponytail portion by teasing, twisting, or scrunching. The juxtaposition of textures creates a sophisticated yet undone look that’s perfect for transitioning from office to evening events. This has become my signature “business in the front, party in the back” style!

25. Messy Side Pony with Barrettes

25. Messy Side Pony with Barrettes

Finish our list with a playful side ponytail adorned with multiple small barrettes or clips. Position your messy pony just behind your ear, securing loosely to maintain volume and movement.

Add several small, colorful barrettes in a random pattern throughout the ponytail for an unexpected decorative element. This whimsical style combines the casual nature of a messy pony with the deliberate placement of accessories for a look that’s both fun and fashion-forward.

The Bottom Line

The beauty of messy ponytails lies in their versatility and the fact that they actually improve as the day goes on. Unlike sleek styles that can fall flat or come undone, messy ponytails embrace natural movement and texture, making them incredibly practical for real life.

Experiment with these 23+ variations to find your signature messy pony style. Remember, the key to nailing the perfect messy ponytail is paradoxical—it requires just enough effort to look effortless. It’s about creating intentional chaos, which is basically an art form in itself!

So next time someone compliments your “just threw it up” ponytail that actually took you 15 minutes to perfect, just smile and say thanks. Some secrets are worth keeping, after all!